Mister Crowley
by VivatRex
Summary: Follows the unconventional friendship of the King of Hell and the Concierge of Crime.
1. Chapter 1

_A/N: This is going to be a collection of chronological scenes of Crowley and Red throughout the time they've known each other. I've gotten a large majority of it done, and I thought I might as well start posting it._

 _Canon details for Blacklist may or may not be fucked-up. I tried my best, but it's hard to keep some of that straight when what's true and what isn't true changes from week to week, practically. I put together what I could with a semblance of coherence, I hope._

 _Also, because it's Crowley, things get a little gay at times, but not so gay that I would venture to call it slash._

 _Anyway, hope you enjoy. I know I'm not exactly catering to a huge audience here, but ah, I had fun with it._

* * *

 **[No. 2 - Mr. Crowley]**

 _March, 1988_

* * *

Raymond Reddington stands in the center of a lonely rural crossroads in Nebraska, and he wonders how it's come to this. To black magic, and things better left in the dark. To dying little girls and burnt stuffed bunnies. To demon deals and scars on his back that he knows very well will never heal.

Life, much like love, is often sad, but sometimes it's funny. He doesn't currently know which category his situation falls into.

With a sigh that should only come from men twice his age, Red kneels down, old cigar box in his hand. Something Sam gave him. A joke and a gift wrapped in one. Sam has a taste for irony, and knowing Red's penchant for only the most expensive Cuban cigars, he deemed it necessary to give him a cigar box that looked like it belonged smuggled away under some teenager's bed, alongside a hastily folded pinup.

Inside the cigar box is a vial of graveyard dirt, the bone of an unfortunate black cat he'd found poking into the dumpster behind Sam's house, and finally, his driver's license, the only picture of himself he has on hand. Frowning at the dirt that's bound to get under his fingernails, Red begins digging a shallow impression in the road.

Once he's four inches down, he gingerly places the cigar box in the hole and brushes the soil back overtop of it. Red rises, drawing himself up to his full height, in spite of the excruciating pain from the burns on his back. He should still be bed ridden, truthfully, but Raymond Reddington is not one to sit and wait while the world crumbles around him.

The best illicit medical professionals money could buy tell him that Elizabeth isn't going to survive the injuries she sustained in the fire. Her burns are mild, but the smoke inhalation... that is a different story entirely.

He has to take matters into his own hands. Today, he will take fate and force it to bend to his will. He can only hope that the mystic he'd spoken to in New Orleans last spring had been truthful when she'd told him of Crossroads demons and deals. He's inclined to be skeptical, it's his nature, but the woman had spoken with such utter conviction... he can't help but believe her.

"Well, well. What do we have here?"

Red freezes when he hears the voice behind him. Rough, British. It's not unlike the sound of someone dragging their fingers through gravel. He turns slowly to meet the newcomer.

Standing five feet behind him is a man dressed in a sleek, all black suit, complimented by a gray paisley tie. He wears a wool overcoat, where he buries his hands. He's clean shaven and his hair is neatly kept. His appearance screams wealth and taste.

 _How fitting_ , Red muses. "I do hope you're a Crossroads demon. I'm afraid I'm quite unprepared for any other supernatural entity."

The man smirks at that, giving Red a mock bow with an extravagant twist of his wrist. "King of the Crossroads, at your service." The man - _demon_ , Red corrects himself - draws back up, brushing nonexistent dirt off of his suit. "The name's Crowley."

"Well, Mr. Crowley, I trust you know why I'm here," Red says. He realizes he should be afraid, being in the presence of a demon, but he's captured by a kind of numbness instead, separating him from his fear.

"Let me guess: wealth?" Crowley inquired, almost sounding bored. He gives Red a once-over with an arched eyebrow. "Dolce Cabana shoes, Armani suit. You've a taste for the finer things."

"I have no interest in material gain," Red replies evenly.

Crowley seems faintly surprised at that. "Not in it for money, eh? What is it, then? Women? Fame?" Crowley gestures vaguely at his head. "Little more hair up top?"

A muscle in Red's cheek twitches at that. He's only nursing a small bald spot, and really, it's hardly noticeable. It's not as if he's going to go completely bald.

Crowley comes closer, only a foot separating them, now. "Or..." the demon drawls. "You want me to fix those nasty second degree burns covering the entirety of your back?" Crowley leans forward and puzzlingly, the demon sniffs Red. "Wait, I take that back. Third degree burns."

"I do need you to heal someone," Red responds. "But not me. A young girl. She's sustained serious brain damage from smoke inhalation, and she doesn't have long left. I need you to save her, if that's within the scope of your powers."

"The question isn't whether it's in the scope of my powers, it's what exactly you'll give me in return for my services," Crowley tells him in no uncertain terms. "You _do_ know how Crossroads deals work, I hope?"

"I understand that traditionally, I would offer up my soul in exchange for your help."

"I'm sensing a _but_ , here."

"I see little point in signing over my soul to you, Mr. Crowley, when it's almost certainly already destined for your domain. I'm here to offer you something that I think will prove far more useful to you in the long run."

"Listening," Crowley says, scrutinizing Red's face.

"One moment," Red tells the demon, holding up a finger. He briefly returns to the beat-up Pontiac he'd driven to the crossroads, a car Sam had been so kind as to lend him while he sorts out his affairs. In the back of the Pontiac, there's a suitcase. Red stares at it briefly, and he hopes, he prays, that it's enough to buy the demon's favor... because if everything is not enough, he will have no choice. He will be forced to make the typical deal.

His soul for Elizabeth's healing, and in ten years, he will be killed and his soul will be taken to Hell. Ten years. Dead at forty. Raymond Reddington is not a man who clings to many things, but he does cling to life. Life is beautiful, and tragic, and compelling. Filled with wonders. He is not the kind to take it for granted, not one single moment, even the most painful.

Even with half of his body being roasted alive and a screaming little girl trapped beneath him, he values it. He values the lesson he is taught. Sacrifice, and its true meaning.

For Elizabeth, he will become an international fugitive.

For Elizabeth, he will take the scars, the agony.

For Elizabeth, he will make a deal with the devil.

He can pretend it's all just guilt over the fate Elizabeth's parents met, or the fact that Elizabeth is now the only living link to the Fulcrum - perhaps she even _is_ the Fulcrum - but he's never been good at lying to himself. He believes in fate, and in some cosmic twist, the girl that was meant only to be a mission seems to have become his north star.

Red grabs the suitcase and returns to Crowley, who is waiting impatiently for him. Red pauses two feet from the Crossroads demon. "In this suitcase is a list of the most powerful men in the United States government. Their dirtiest secrets, and every pressure point they have. With this knowledge, you could practically seize control of the United States government overnight."

Crowley seems faintly impressed. "You're offering me power," he surmises.

"I am," Red confirms.

Crowley hums, lips twitching in slight amusement. "Brilliant scheme. But I'm afraid there's a flaw in your plan, mate." Red's hand is suddenly empty. Crowley is now holding the suitcase. "I am a _demon_ , remember? I want something, I take it."

"I suppose I should have seen that coming," Red concedes. "But the contents of that suitcase, that's not the only thing I'm offering you."

"Unless your soul is in the payoff, darling, I can't claim to be interested," Crowley replies.

"It is, in a manner of speaking. But not just my soul. My body, as well."

He doesn't miss the lascivious trailing of eyes down the length of his body. "While the proposition is tempting, a good roll in the hay doesn't-"

"I didn't mean in that sense," Red cuts across him. While he considers himself adventurous - he's played doctor with both sexes in his time - getting into bed literally with a demon is something he'd rather avoid. "I have a network of contacts and informants that stretches across the globe, a veritable slew of resources. And most importantly," Red inhaled deeply, "I will do anything you ask of me for the remainder of my life, should you accept this deal. To couch it in basic terms: you will own me, and when I die - _naturally_ \- my soul will be yours."

Crowley chuckles. "You really are desperate, aren't you?"

"I'm willing to do what needs to be done to save the girl's life," he answers. "Waive the ten year deadline, and I will serve you for the remainder of my years."

"You've an awfully inflated sense of self-importance," Crowley observes. "Who says I need a human to do my dirty work for me?"

"You know my offer, Mr. Crowley. I can't control whether you take it or not." Red adjusted his sunglasses. "The ball, as they say, is in your court."

Crowley narrows his eyes at Red, lips thinning. The demon takes almost a full minute to weigh his options. When finally he speaks, he says, "Mr. Reddington, I find you fascinating. I'll take your deal." Crowley inserts himself into Red's personal space. He expects to smell sulfur, but a fine cologne is all that meets his nostrils. "But remember, when you die? You come to Daddy."

"Understood."

Crowley smiles. "Fantastic." The demon snaps his fingers, and the suitcase vanishes from his hand. Crowley reaches inside of his overcoat and pulls out a bound scroll. "And now it's time for my favorite part." The scroll unfurls. It's so long that it piles between Red and Crowley's feet. "This shouldn't take long at all," the demon declares cheerfully.

* * *

"Mr. Crowley, there's nothing in here that prevents you from killing me before my time and taking my soul."

"Ah, must've slipped my mind."

"There's also nothing to indicate that Elizabeth's healing will be permanent."

"I see you have an eye for loopholes. That's unfortunate."

"I request that you change the wording. Elizabeth's permanent good health is imperative."

"Fine, fine."

After nearly three hours, their negotiations are finally complete. As the sun sets and paints the world orange, Red signs his name on the bottom of the nearly twelve foot long contract, which is now covered in corrections, all made in red Sharpie. Once it's signed, the contract rolls itself back into scroll form.

Crowley smirks at him. "And now to seal the deal properly."

"Like the Romans do, correct?" Red tilts his head.

"I do love an informed customer," Crowley practically purrs as he slides a hand around the back of Red's neck and pulls him forward. A moment later, the demon's lips are on his. He feels an itch in his skin, like the words of the contract are being scrawled into his flesh. Crowley's kiss is not delicate, but it is professional. It is done with impossible focus, and he can feel it, can feel the kiss binding them together.

Crowley tastes like smoke and scotch. Red's had worse.

When they break apart, Crowley is wearing a smug grin. "Enjoyed that, did you?" he asks, noticing the flush of Red's cheeks. "Don't worry, darling. Everybody does."

"I believe it's time for you to hold up your end of the bargain," is Red's only reply.

"Of course. Where's the girl?"

Red rattles of Sam's address. Crowley nods, then sets a hand on Red's shoulder. He feels a tugging deep in his stomach, an almost painful kind of compression, as the two of them suddenly blink out of existence.

When Red's senses return to him, they're next to Elizabeth's bed. Or rather, the bed in Sam's guest room that the young girl has occupied for the past three weeks. A cot nearby is where he's been recovering. Doctors visit everyday to attend to the both of them. Red receives more care than Lizzie, due to the severity of the wounds on his back, and the fact that besides changing her feeding tube and IV, there's little they can do for her condition.

Elizabeth is hooked up to a slew of machines that force her body to continue. Her ventilator is loud, and a constant reminder that she cannot breathe on her own.

"So, this is she?" Crowley asks, approaching Elizabeth's bedside. The girl is a pale, delicate thing, looking small and fragile underneath all of the tubes and wires. The demon reaches out and brushes a lock of hair out of her closed eyes. Red's not sure he likes the demon touching Elizabeth like that.

"It is."

"What's her name?"

"Elizabeth."

Crowley leans down, eyes intent on the four year old. "Well, Lizzie," the demon says, almost softly. "Aren't you lucky that someone's willing to sell themselves in order to keep you alive?"

"Mr. Crowley-"

"Relax, Raymond. I'm merely savoring the moment." He narrows his eyes at Elizabeth. "Isn't that interesting?"

"What?" Red asks, not liking the fascinated expression on Crowley's face.

"I've never seen a four year old with a soul this tainted before," the demon elaborates. "She's killed already, hasn't she?"

Red says nothing, but his silence speaks volumes.

"Dra-ma," Crowley chimes in a sing-song voice. He sets his hand on Lizzie's forehead. The demon closes his eyes for a moment.

And then, the machines monitoring Lizzie's heart rate and breathing jump to life. Color floods her skin, and she shifts in her bed as her mind and body reawaken. Crowley seems annoyed by the inane beeping. With a wave of his hand, the machines vanish.

"She's healed," Crowley states needlessly. "She should wake in a few minutes."

A wave of relief sweeps over him as he takes in the sight of the healthy child. Elizabeth is alive and well, and any cost he must pay in the future for his actions will be worth it. Elizabeth is alive. At present, that matters more than anything else.

"Thank you," Red tells Crowley, and he means it.

"Thanking the demon who owns your soul?" Crowley snorts. "I know there was a reason I liked you. Oh, by the way, did you a bit of a favor - I wiped her memory of that little... incident."

Red tenses at that. Crowley invaded her mind?

"Oh, don't get your knickers in a twist. No damage done. It's all for the best, scout's honor."

Red circles around to Elizabeth's other side. He gingerly lifts her pencil thin arm. There's a bandage covering her hand and wrist. The only area that was burned during the fire. Red had been able to shield the rest of her.

"Can you heal this as well? It's bound to scar."

"I've already numbed it. She won't feel any pain." Crowley smirks. "But I think I'll leave the scar... as a reminder to both you and her."

Red looks up at him sharply. "What do you mean?"

"I mean... I think this girl's got a very bright future ahead of her," Crowley says. "And someday, I may just pay her a visit."

Red's stalking towards Crowley in an instant. "That was not part of our contract-"

But it's too late.

Crowley's already gone.


	2. Chapter 2

Red doesn't see any sign of the demon who owns him for the next six years.

It's been so long, Red begins to wonder if the whole experience wasn't some vivid fever-dream, and Lizzie managed to heal simply through the grace of God. It's certainly a more favorable option than the idea of a demon having full-claim on his soul.

But Lizzie is just too healthy and breathes too well, and he hates that the demon's nickname for her stuck... but damn it if it doesn't fit her. He watches her from afar, checking in on her on occasion, visiting both Lizzie and Sam. He'll only be able to do this for a year, maybe two. Lizzie can't remember him as an adult, because that will raise questions.

Questions like, "Sam, why were you friends with an internationally wanted criminal?"

The fact that he sold Navy secrets to the highest bidder doesn't come out until '93... but the thing is, while he did trade information to several countries in exchange for security, resources, and money, of course, there are certain organizations that hold state secrets that he never spoke to.

He can only assume it was Mr. Crowley.

Mr. Crowley, who has his suitcase and in turn knows things that even the POTUS isn't aware of. Apparently the demon is capitalizing on it, as well. Red can hardly blame him. He gave him the suitcase knowing full well that it would eventually fall back on him. He'll gladly take the fall.

The country he once served puts him on the Most Wanted list, and he becomes a fugitive.

By the time Lizzie is out of kindergarten, he knows he can't visit anymore. The last time he sees her is her sixth birthday. Sam tells him she's in a princess phase, and Red buys her a dress worthy of a Disney princess, periwinkle and appropriately covered in sparkles. The little girl tries on the dress with glee, spinning in a circle before racing towards him and hugging him tightly.

Red thinks of his own daughter, and tries not to break down right there among the pink streamers and birthday cake.

Red says goodbye, and knows it will be a very long time, if ever, before he's face to face with Elizabeth Scott again.

He thinks of her often though, and he keeps an eye on her progress. She does dance for a few years, and he makes it to as many of her recitals as he can, even it means taking his jet from Doha to Nebraska. Because he cares. He cares far more than he should, and it's his weakness, perhaps, his greatest weakness. _Lizzie_ is his greatest weakness.

By the time she's nine, Red's confident she will one day be his downfall. Maybe it's prophetic, maybe it's just common sense, but he knows that Elizabeth Scott is going to destroy him.

Everyone gets destroyed in the end, but few get the chance to choose who does the destroying. He can't think of anyone he'd rather have tear him down.

This is what's on his mind as he sips an absolutely delectable strawberry daiquiri on a white sandy beach in the Caribbean. He's here to oversee an arms trade, but his services aren't required until tomorrow.

To his credit, he barely flinches when he hears the voice next to him: "Mind if I have a sip?"

Red's eyes close for the briefest of moments. He tries to remain calm.

"It's almost as if you're not happy to see me."

Red sighs heavily, removes his sunglasses, and turns to look at the being now occupying the beach chair next to him. Crowley looks exactly as he did five years beforehand. All black suit, immaculate appearance, gray paisley tie. The heat doesn't seem to affect him, and Red isn't surprised by this.

"Truthfully, I was beginning to think I'd imagined our little arrangement. Or beginning to _hope_ , anyhow," Red admits, and he passes the daiquiri to Crowley, because he doesn't care if the demon is kidding or not.

Crowley accepts it. "Sorry darling, I'm the real deal. Lucky thing too, or itty-bitty Lizzie would still be a vegetable," he commented, swishing around the drink before taking a deep sip. "Hmm. Not bad. How _is_ Lizzie, by the way? I trust you've been keeping an eye on her?"

"I trust you've been doing the same, so why ask?"

Crowley simply chuckled, handing him his drink back and snapping a glass of what appeared to be scotch into existence.

"Not a fan?" Red asks.

"I prefer my brand." Crowley raises the glass. "Glenncraig. Aged thirty years at least. Been drinking it for centuries."

"Ah, Glenncraig. I knew a man once by the name of Torrian, lived in the backwoods of Scotland, near Canisbay. He brewed the stuff, was _very_ particular about his process, so much so that he refuses to pass the craft on to any of his sons, as he's convinced they'll muck it up somehow. Though, I have to say, his own mix is by the far the best I've had. That perfect balance of citrus and tobacco, with that warm burn that's just enough to stoke the fires... nothing compares."

Crowley seems pleased by his knowledge as he nurses his drink. "You're a man of refined tastes. I can respect that. Though fedoras, _really_?"

"They work in any weather, can match any outfit, and allow for anonymity. The perfect accessory," Red says, adjusting his hat. "Not to mention, it strikes one hell of a figure."

"Mate, no one looks good in a fedora."

"Are you here to give me fashion advice, Mr. Crowley, or are you here to collect?"

"Why not both?" Crowley drains his Craig quickly, and then the glass disappears. The demon rises to his feet. "I'm looking for something. It occurred to me you might just be able to help me find it, with your seemingly endless resources."

"What is it you want?"

"A gun," Crowley says. "A very special gun. One made by Samuel Colt himself." He reaches into his overcoat and pulls out a manila folder. He hands it to Red. "Everything I know at present is in there. Call me when you find it, but don't go after it yourself. I have plans for it."

"May I ask what you want with it?"

"You can ask, but I won't answer."

Red's lip twitches, and he doesn't like the idea of doing dirty work for a demon without any knowledge of what consequences it could reap. Then again, he doesn't really have a choice, does he?

"Very well. I'll see what I can do."

A ghost of a smirk passes over Crowley's features. "Call me." Crowley swoops down and pecks him on the cheek. Before Red can even be startled, Crowley's gone, leaving him alone.

He wonders how he's supposed to call him when he doesn't have his number-

And then suddenly, there's a screaming pain his arm. He flinches, letting out a pained exclamation, eyes going to the afflicted area.

There, gleaming in blood and carved into his very flesh is the number 666.

"Oh, you have got to be kidding me."

The same pain rips through his other arm, and this time the inscription simply reads "I'M NOT" in capital letters.

Red grimaces. He's going to be wearing long sleeves for awhile.

* * *

This Colt of Crowley's is not easy to track down. It's been passed around from families to museums, private arms collectors to gun showmen. It's gone off the map for years and years only to resurface on the other side of the country. It's stayed primarily in America, which narrows his search, but it's still a veritable bitch to find.

But he puts all he can into it, because he'll admit a part of him fears what Crowley will do to him if he fails in the task assigned to him... or more importantly, what will happen to Lizzie. These past few years, he's enjoyed the luxury of freedom, of answering to no one, of always being in control of his own life. The realization hits him, though, that this isn't truly the case. Whether he likes it or not, he serves Crowley... and he will be serving Crowley until his dying day.

He finds the Colt sixteen months after his meeting with Crowley in the Caribbean. He's received no calls or visits from the demon urging him to work faster, so it seems he's content to wait as long as needed for Red to locate it. Red vaguely wonders if it's some kind of test.

Half-sure it won't work, Red dials 6-6-6.

Ring... ring...

"Raymond. I hope you have good news for me."

Red doesn't want to know how Crowley is already aware it's him before he's even had a chance to speak.

"I do. Daniel Elkins, Manning, Colorado. To my knowledge, he's the last one to have the Colt in his possession. I had an associate search his house discretely on one of the few occasions he wasn't home, and he found it."

"You didn't have him remove it, did you?" Crowley asks sharply.

"I did not."

"Good," Crowley says firmly. "You're less inept than I thought."

"Thank you. I think. Now before you go, there is one additional matter I'd like to discuss."

"I'm waiting with bated breath."

"I know you still have some of your men watching Lizzie. I'd like to request that you cease all surveillance on her."

"Why ever would I do that?"

"Because I don't like the idea of demons watching her."

"But I have plans for her," Crowley said, and he can hear the smile in his voice, and it makes Red's blood boil.

"What purpose could one little girl possibly serve?"

"I'll let you in on a secret: the fate of the world itself rests on the shoulders of what are now two boys, one who's sixteen, and one who's twelve. Age doesn't exclude you from being relevant to the grand plan, Raymond."

"You guaranteed me her safety," Red growls, patience lost.

"Oh, she'll be safe," Crowley told him. "Don't worry your head about it, sweetheart. I've got everything under control. Kisses."

The demon hangs up, and Red resists the urge to smash the landline against the wall.


	3. Chapter 3

Years pass. Lizzie sprouts up remarkably fast. She goes from a smiling, gap-toothed child to a rebellious teenager who wants to dye her hair bright red against Sam's wishes. Sam calls him when he can and tells him about her, and Red listens with rapt attention. It's the only calls he has that don't deal with death and misfortune, so he relishes them.

Lizzie is a handful. Given her mother, he wouldn't expect anything less. But she's smart, wickedly smart – he's seen her grades, and he's already lining it up for her to get a full scholarship to college – and he knows she's going to go far. She's strong, volatile, sharp as a tack... he feels a certain pride, when it comes to Lizzie, an inexplicable one. Like a doting father, even though that's very far from what he is.

He hears nothing from Crowley until a year into the new century. He's with Dembe in a hotel suite in Azerbaijan, currently on the run from an anti-military syndicate that he's had a run of bad luck with. Meeting Dembe has been perhaps one of the brightest points of the past few years for him, in spite of the circumstances he pulled the boy out of. He is quiet, yes, but kind-hearted and extremely loyal. Dembe is determined to protect him to his last breath, and Red can't find it within himself to discourage Dembe from that mission.

Red enjoys his company. He says little, but always listens, a quality that is hard to find and he makes sure to value as much as possible.

Crowley appears out of nowhere, occupying a space that was empty the second beforehand. Said space being Red's lap, that is. Dembe, bless his reflexes, is out of his seat and holding a gun on the demon in the span of one breath, some kind of Kenyan curse leaving his lips.

"Ah, Raymond! You finally got some decent help, I see. So hard to find these days, bla bla bla..." Crowley is effectively straddling him, and the Crossroads demon winks at him before sliding off and rising to his feet.

"Do not move," Dembe orders, flicking off his safety.

"It's quite alright, Dembe," Red says, holding up a hand. "Mr. Crowley is an... old associate of mine."

Dembe does not lower his gun, and his dark eyes are bright with suspicion. "What is he?" he asks, and really, Dembe is so much smarter than most anyone gives him credit for.

"An utter and complete monster," Red answers. "And I mean that in the very literal sense."

"Flattery will get you everywhere," Crowley comments, wandering over to the windows that line one of the walls of the presidential suite and gazing out over the skyline, hands in the pockets of his overcoat. "I'd like this discussion to be private, so if you could send your errand boy out..."

"Dembe is not my errand boy," Red says firmly. "Anything you say to me can be said to him." Trust is a new thing for Red, but he's trying it with this boy, he really is. If Dembe is to accompany him everywhere, he will eventually learn the nature of his arrangement with Crowley. Might as well get the matter out in the open as soon as possible.

"You sure you want your friend to know just what you get up to in the dark, darling?"

Red levels a cool glare at Crowley's back. "Dembe's seen far worse than you in his time, Mr. Crowley."

A snort from the demon. "Oh, I highly doubt that. But have it your way." He still doesn't turn. "Do you remember that little chat we had a few years ago? About those two boys?"

"The boys that supposedly will decide the fate of the world?"

"You _do_ remember. Good, because they're what I want your help with. I need them followed. Both of them. By humans."

"Is there some reason your demons can't perform such a task? They certainly do a good enough job of following Lizzie," Red says, and there's anger in his voice. It has no effect on Crowley, unsurprisingly.

"See, the rub with that is, there already _are_ demons following them... and they're not mine, nor would I trust mine to do so discretely." Finally, Crowley turns. "Sam and Dean Winchester. Dean Winchester is... well, truthfully, I've no idea where he's gotten off to at present. Sam Winchester is currently attending Stanford. Pre-law, full-ride. Lad's smart as a whip." Crowley's head tilts a little. "Sam's just a bit older than Lizzie, you know. We should hook them up. Quite the power couple, wouldn't you say?"

Red schools his face to appear professional, but on the inside, he in no way wants Lizzie involved with anyone the forces of Hell have any kind of personal interest in... though arguably, one particular denizen of Hell already has an interest in her. "Follow, observe, and report, I assume?"

"Naturally. I've been keeping an eye on you, seeing how your little criminal empire's growing by the day... I'm sure you've got the manpower to spare, Mr. Concierge of Crime."

It's a nickname that's just starting to gain renown in the media, and Red doesn't like it, but he supposes it's better to have a reputation as one who deals with those who deal death rather than one who deals death himself.

"I'll have my best on it. No interaction?"

"None."

"Fine. How frequently should I update you?"

Crowley thinks for a moment. "Every week on Dean, once a month on Sam."

"Your number is the same, I assume?"

Crowley laughs. "Always." Crowley checks the time and frowns. "I'm afraid I'll have to cut this short." His eyes flick to Red. "Absolutely _lovely_ to see you again, Raymond. I look forward to next time."

And then, he's gone.

Dembe still has his gun out, and his eyes are bugging out of his head. He stares down at Red, nostrils flared.

"Raymond–"

"Sit down and have a drink, Dembe. This is going to be a long conversation."

* * *

It's through having the Winchesters tailed – Dean Winchester, specifically – that Red begins to learn the true nature of the world he lives in. He knew of demons, heard tales of angels, had been relatively sure he'd encountered a ghost or two in his time... but he was never aware of the extent of supernatural entities running amok on earth until he got his first few reports on Dean Winchester, and his father, John Winchester.

Werewolves. Vampires. Ghouls. Something called a Kitsune that Red spent an afternoon in a library in Venice trying to find out more information on. The Winchesters leave a trail of corpses in their wake, most headless, some shot with silver bullets. When bodies aren't found, graves are desecrated and remains salted and burned.

Quickly, Red learns that Dean and John Winchester are 'hunters' – individuals who dedicate their lives to the eradication of paranormal threats.

(The people Red has following the Winchesters are very good at what they do.)

Red is, and always has been, a naturally curious person. He also prides himself on being as informed about the dealings he involves himself with as possible. It's because of this that Red begins digging deeper into the dark underworld of the supernatural. Learning all he can from readily available resources at first, and eventually moving onto shady back-alley deals for rare lore books that make Dembe's face draw in all the wrong ways.

Dembe doesn't at all like what Red's getting into, being understandably superstitious as he is, but Red tells him that they need to know who exactly they're dealing with. He spends seemingly endless time in hotel rooms all over the world with the blinds drawn and his feet up, flipping through this and that. _Binsfield's Classification of Demons_ becomes his favored morning reading material, for a time. Something about the occult and coffee, he supposes.

By the time Lizzie is in college, he considers himself a near-expert on all manner of things that go bump in the night. If anything, it makes him worry for Lizzie's safety far more, knowing that there is so very much out there that has the potential to hurt her. And worse yet, she's a prevalent blip on the radar of the King of the Crossroads.

Things like this keep him up at night, truly.

He dutifully calls every week and keeps Crowley abreast of Dean's movements, and once a month, the call contains information about Sam as well, though the other Winchester isn't a tenth as interesting. Sam, for all appearances, is a boy scout. Dutifully attending his classes and living with a beautiful young woman by the name of Jessica Moore.

This goes on for four years, and strange as it is, Red becomes used to talking to Crowley. For the most part, their conversations remain short, concise, and professional, but Crowley will occasionally ask him about Lizzie, or a recent deal that Red's made that the demon has caught wind of in someway. When it's about business, Red doesn't mind sharing. Crowley, for all his faults and eternal damnation, does understand what it is to be an illicit businessman. They're two sides of the same coin, but Red only deals in souls in the metaphorical sense.

When Crowley inquires about Lizzie, Red usually tenses and ends the conversation. Because damn it, he doesn't like it. Doesn't like how her name sounds on his lips. Doesn't like the fact that he knows Crowley has demons watching Lizzie. Watching her walk from her dorm to her classes, watches her with her friends, hell, probably watches her _sleep_.

So one day, Red decides to try something.

He teaches one of the guards he has watching Lizzie from afar an exorcism. He instructs him that if it ever appears that Lizzie is being watched by someone other than him, that he's to attempt that before gunfire or a knife.

Just as Lizzie's finishing up her third year, Red gets a call from Crowley.

"You exorcised one of my bruisers. I'm impressed. You keep your men more well-informed than I thought."

"I've been making an effort to be more aware of your world. Especially given that world poses a threat to Lizzie."

"You think I would hurt Lizzie? She's like a daughter to me!" Crowley says, all mock-affront and sarcasm. Red grits his teeth. "Fine, Raymond. You've made your point. I'll keep my boys away from your little lost lamb... for now."

"Forever, Mr. Crowley."

Crowley laughs, then hangs up.

As an act of revenge, Red doesn't call the next week, but this only earns him, yet again, another abrupt lapful of Crowley. Also, the demon ends up drinking two thirds of the bottle of Pinot Grigio he'd ordered from room service.

"I was worried something may have happened to you," the demon says, looking so utterly like the devil he is, it's like his vessel isn't even there.

"I'm sure," is Red's dry response.

So Crowley stays, and he drinks, and they talk about everything and nothing, and eventually Crowley does squeeze the now two weeks backed up report on Dean out of Red, though it's after Red's had enough wine to add a permanent blush to his cheeks. Crowley actually appears to be somewhat drunk, which surprises Red. He hadn't known demons were capable of such a feeling.

At one point, once he's thoroughly inebriated, Crowley says, "You're going bald, love."

Red throws his fedora at Crowley. Red doesn't remember much after that, but the next day, his fedora is nowhere to be found.

Red hates to admit it, but he has grown accustomed to Crowley and his snark, his wit, his threats and innuendo. Crowley is mad, and most certainly the most powerful and evil being Red's ever encountered, but he is also infinitely charming. He spends his time in the presence of many monsters, and after all these years on the run, hiding in shadow, he knows he's a monster himself. Possibly the worst of them all.

He's doomed to the company of demons, so why not carry on with a literal one? A literal one who is at least far more intellectually stimulating than most of the brutes Red encounters on a daily basis.

Dembe still passionately hates Crowley.

Red knows this is something that will never change.

* * *

In October of 2005, things turn... concerning.

He has something to report about Sam, finally.

"Mr. Crowley," Red says, and yes, even after pushing twenty years, he's still calling the Crossroads demon that. He doesn't know if the demon has ever caught the Black Sabbath reference. "I have news."

"Sam Winchester's girlfriend is dead. Toasted on the ceiling of their apartment, which is now burned to the ground. Sam is back on the road with his dear brother Dean."

He's never heard Crowley sound so dejected.

"Yes, how did you...?"

"Who do you think was responsible?"

Red is silent for a moment, then asks, "Did you do this?"

"Me? No. Hell? Yes."

"You sound less than happy about this turn of events."

Crowley inhaled deeply. "And so it begins."

"Dare I ask... so _what_ begins?"

"The end of the world as we know it."

With a click, Crowley hangs up.


	4. Chapter 4

Red doesn't hear from Crowley for three years. As is expected, when he does see Crowley again, he appears at a most inopportune time.

Mrs. Loretta Traven is an exquisite woman, undeniably. She also just so happens to be the wife of a British diplomat whom Red knows has connections to a Ukrainian militia that is responsible for significant losses of manpower he's sustained recently. She is a pressure point, one he fully intends to exploit. The closer he gets to the lovely Mrs. Traven, the closer he gets to whatever skeletons are in Marcus Traven's closet... the very skeletons he will use to blackmail Traven into putting a permanent end to the barbaric guerillas serving his needs.

A line of dominoes. As always, it's all about pushing over the right one, at the right time. Though as he presses Loretta against the door of his hotel room, beautiful penthouse overlooking Trafalgar Square, all mist and birds this time of year... well, he will admit that this isn't exactly how he planned to go about getting to Traven.

Her lipstick is a curious shade of maroon. He knows his face - and perhaps other places, depending - will be covered in it by morning.

His prospects for the night are sunny, until-

"What the hell!?"

He pulls up from Loretta's neck, and she's staring behind him, brown doe eyes wide and broad lips open in shock. Red turns, and over his shoulder, he sees him. He closes his eyes, searching for patience.

"Raymond. Been too long, darling."

Crowley sits in one of the fine chairs near the electric fireplace, legs crossed and ever-present smirk curving his mouth. There's a glass of Craig in his hand, glimmering amber in the firelight. The bottle is on the nearby table, waiting.

Red turns back to Loretta, sighing. "My dear, though I hate to ask... rain check?"

She looks at Red as if he's lost his mind. He most likely he has. "Who is he?"

"Oh, I know Raymond better than he knows himself," Crowley chimed. "Our relationship is, how to put it delicately..." The demon tilted his head to the side in mock consideration. "Have you ever seen Wild Kingdom? Those insects that rip their partner's heads off after copulating?"

Loretta is mildly disgusted by that. "Goodnight, Mr. Reddington," she says icily, slipping out of Red's grip and promptly exiting the hotel room. The door shuts hard and loud behind her. Red grimaces. Pity, that. Crowley may have just set his plans back by weeks, if not months.

"You seem to have made a habit of dropping into my life at times of utmost inconvenience," Red says as he strips of his overcoat and drapes it over the back of the chair next to Crowley. He deposits himself in the chair, mirroring the demon's pose.

"Don't pretend you're not happy to see me," Crowley replies. He snaps his fingers, and a glass filled with three fingers of Craig appears in front of Red.

"I find myself happier to see your preferred brand," Red says dryly, scooping up the glass and not hesitating to put it to his lips. He drinks deeply. He has the distinct feeling that this is going to be a long night.

"Trying to drink your feelings? That's not healthy, mate."

"Don't beat around the bush, Crowley. Coy doesn't look good on you."

"Au contraire. Everything looks good on me."

"Humble as ever, I see."

"You're not exactly one to lecture on modesty, are you?"

Red sipped at his drink. "I believe the saying is, 'do as I say, not as I do', yes?"

"All of the quotes and profundities in your vocabulary, and you go with that?" Crowley scoffed. "Someone's losing their touch."

"Mocking my rhetoric still isn't telling me what you want from me."

"Who says I have to _want_ anything?" Crowley counters.

"You're a demon. From what I've come to grasp about you personally during our time together, wanting things is the very core of who you are. You want souls, you want power, you want wealth, you want... well, you're never one to aim low. You want everything, and what's left after that, too."

Crowley simply narrows his eyes at Red. "I never knew I was on your mind so much, Raymond. I _do_ hope you haven't been having unclean thoughts."

"Nothing that would make you blush, I'm sure."

"You have me there." Crowley drummed his fingers on the side of his leg. "Well, if you must know... I needed a sympathetic ear."

"And you've come to me to unload your troubles?" Red asks, trying to not sound incredulous. He knows he fails, at least in part. Crowley doesn't seem the type to ever need a sympathetic anything.

"Well, if a certain pagan god I know had bothered to pick up his bloody phone, I wouldn't be here. But alas, he's nowhere to be found, and I thought to myself, why not drop in on an old friend?"

"Would you really venture to call me that?"

"Why not? We've known each other for ages, been through thick and thin-"

"No matter our history, I'd argue that a slave owner and his charge can never use the term 'friends' to describe their relationship," Red ponders. He's not being antagonistic, just making a valid point.

"Slave's such a harsh word, wouldn't you say?"

"What term would you prefer? Indentured servant?"

"Friends with benefits?" Crowley asks with a lecherous arch an eyebrow.

Red takes off his hat, setting it on the glass coffee table with a long exhale. "Well, I'm never one to turn away someone in need, even if that someone is a demon who more or less owns my ever-living soul." Red gives Crowley a tight smile. "By all means, tell me what's troubling you."

"The end of the world as we know it is what's troubling me," Crowley told him, wasting no time.

"That's what you said the last time we spoke... I had hoped you were overexaggerating," Red says, brow drawing together.

"Not in the slightest." Crowley downs the rest of his glass with gusto. "I mean the authentic, cataclysmic, bloody end of everything and everyone. Armageddon. Fire and brimstone, cats and dogs living together... mass hysteria."

"And what, pray tell, will bring about this supposed Judgment Day?"

"Haven't you ever read Revelation?" Crowley asks.

"As a boy, yes, but you'll have to refresh my memory on why exactly we're facing the ultimate end."

"Michael and Lucifer. The final battle... Heaven vs. Hell, winner takes all, Earth and the human race loses no matter what."

"Mass chaos, death, and destruction. Surely that's something you're in support of, given your species."

"Species," Crowley spat out the word like poison. "My _species_ is quickly becoming the bane of my immortal existence."

"And why is that?"

"Because I don't want the bloody apocalypse!" Crowley's up out of his chair now, pacing, more erratic and irritated than Red's ever seen him before. Gone is the unendingly calm, consummate businessman. Crowley's thumb pinches his lower lip, his eyes distant and distracted, and it's the closest to human Red's ever seen him look.

"A demon who doesn't want Armageddon," Red muses. "Now that's something I didn't expect. _Fascinating_ , really. I have to ask... why?"

"I'm in _sales_ , Raymond. I deal in souls. It's a simple equation. If there are no souls left, because all of the humans are dead... then what purpose do I serve?" Crowley asks. "None. I'm pointless. Worthless," the demon bites out, and Red can almost swear he hears an ' _again'_ hiding at the end of the sentence, unspoken but not unsaid.

"The Crossroads Department has no point in a world with no humans to corrupt," Red reasons.

"Exactly! So what am I supposed to do, then? Just follow orders? Just let everything get torn down? For what? So we can let some pretty boy archangel with daddy issues wipe out our entire race as soon as the humans and the angels are dealt with?"

"Why would Lucifer destroy the demons?" Red inquires with a tilt of his head. "From my knowledge of Biblical lore, he created your kind."

"You think that makes any difference to him?" Crowley snaps. "We were... we were just a way to spite his Father. He took God's favorite creation and twisted it. Lucifer hates humans, what must he think of us? I'm quite sure he sees us as nothing more than bottom-feeding abominations. When he's done burning the world down, we're next. And there's only one thing I value more than my position, and that's my life." Crowley's fists clench and unclench at his side. "I'm not giving that up for anything. Not for Lucifer and his bloody cause, not for Lilith... not for anyone."

"Lilith," Red repeats. "Not... _the_ Lilith?"

"The Lilith," Crowley confirms. "The demon currently in command of Hell's forces until we manage to drag up Lucifer, which if everything goes to plan, will be about six months from now."

"So... she's your boss."

Crowley doesn't respond.

"Hard to imagine you at anyone's beck and call."

"I'm her lieutenant," Crowley says it at length. "Her second-in-command."

Red's eyebrows raise in surprise. "My, my. I knew you were powerful... I didn't know you were so high up in Hell's hierarchy, however."

"Shocking isn't it?" Crowley says. "I was always underestimated, ever since I went to Hell. Even after being plucked out of obscurity by Lilith herself and chosen to lead the Crossroads demons when I'd barely been off the rack for more than a few decades, I was..." Crowley shook his head. "Nothing but the damn Terms and Conditions guy. Alastair, well, he has his 'art', and Astaroth had the black witches, and Azazel had his Special Children... then there's me, and even though _I_ provided our army, _I_ was the one damning souls... I was always overlooked. But now? Now, they're all dying off. And who's left? _Me_."

"I think this only leaves one question, wouldn't you say?" Red asks, crossing his legs and taking a sip of his Craig, watching the demon intently. Crowley shoots him a narrow-eyed, curious look, a sign to continue. "What will you do? Lay down and die, or fight?"

"Fight," Crowley says. "What do you think I've been doing? With the Colt, the Winchesters? I've been trying to slow down the process as much as I can. Left a trail of breadcrumbs for John Winchester so he could find the Colt, let him out of Hell long enough to save his idiot sons, his idiot sons who I managed to put in the right place at the right time to kill Azazel... and, of course..."

Crowley reaches into his suit jacket and pulls out a revolver. Red quickly identifies it as the Colt.

"Lilith thinks it was destroyed, but she's wrong. And this?" He turns it, and the silver barrel catches the light. _Non timebo mala._ Fear no evil. "This could be my trump card. _This_ could kill the devil."

"I see why you've taken such an interest in the gun now. But when I say fight, I don't mean covertly working against Hell while still dutifully serving your masters on the surface. There will come a time, likely soon, that you'll have to choose a side."

"What am I supposed to do, turn against Hell? I'd have every demon and angel in all Creation after me!"

"The way I see it, there are three sides in this equation: Hell, Heaven, and humanity. It would only make sense that you would choose to fight with the third, should you decide to stand in the way of Judgment Day."

"What, work with the Winchesters? As if they'd have me."

"Surely it's a better option than working towards your own demise with the rest of the demons," Red reasons.

Crowley returns to his chair, seeming deflated. "You can't fight city hall," the demon says.

"The tides of change eek and ebb, Mr. Crowley. You need to decide now if you want to move with them, or be swept away by them."

"Well isn't that just bloody profound." Crowley pours himself another glass of Craig, throwing his feet up on the coffee table. "I'm staying here tonight. I need a break." It's not a question or a request, but Red nods his assent anyway.

"Demons don't sleep, do they?"

"Not usually."

"Pity."

"Why is it a pity? It's a waste of time."

"If you don't sleep, you don't dream," Red replies.

Crowley seems troubled by that.

They spend the rest of the night discussing everything from the nature of good and evil, to the Winchesters, to their own respective plots and agendas... eventually the conversation once more turns to Lizzie. Red tries to steer the demon away from the topic, but something he says sticks with him.

"You need to have someone in her life, steering her straight, keeping her safe. Not someone just watching, you need to have someone with her," he says after a generous gulp of Craig. "It's time to take it to the next level, my friend."

Red hates to admit it, but Crowley's not wrong.

Once the demon departs the next day, Red makes a few calls.

He hears the name Jacob Phelps for the first time.


	5. Chapter 5

That May, Crowley shows up in Red's current home: a tiny bungalow in Martha's Vineyard. He'll only be here for another week, two at the most, but of all the places he's recently stayed, he prefers this one. It's calm, and peaceful, and he always has enjoyed the sound of seagulls.

After a walk on the beach, he returns to the bungalow smelling of salt and with sand in between his toes. Upon opening his front door, he sees a familiar shape sprawled out on his sofa.

The King of the Crossroads is, as he soon finds out, piss-drunk.

Crowley's suit is disheveled, his usual control shattered. Red gets him out of his suit jacket and away from the bottle of Craig gripped in his hand. He's muttering something about 'bloody Moose' and cages, and Red's just shocked someone who isn't human could get so thoroughly plastered.

At a loss on what else to do for the demon, he hauls him into bed, tucks him in, and turns out the lights. Red falls asleep on the couch that night, after a bowl of New England's finest clam chowder and several hours with the newest lore book he's acquired. This one is about the Heavenly Host. If what Crowley says about Judgment Day is true, he needs to be prepared.

He's reread Revelation eleven times since he last saw Crowley. He won't face the end of times blind.

He wakes the next day when Crowley walks into the living room. Red is a notoriously light sleeper, and just the press of the Crossroads King's bare feet on the wooden floor is enough to jar him out of his slumber. He cracks open one eye and tilts up his fedora so he can view the disheveled demon in full.

Crowley looks strange like this, absent his jacket. His tie is loosened, his feet are devoid of his Italian loafers, and the sleeves of his button-down are rolled to his elbows. He seems almost like a man, less like a monster in an expensive suit.

"Demons can't get hangovers, can they?"

Crowley shakes his head. "No. Handy, that."

Red sits up, pats the couch next to him. "Well, come on then. Something is obviously troubling you. I can provide an attentive ear."

Crowley shuffles over and practically collapses next to him. The demon runs a hand through his hair, staring blankly at his shoes. "They did it."

"Who is they, and what did they do?"

"The Winchesters. They let Lucifer out of his Cage."

"...The Winchesters did that? Not Hell?"

"Through a string of clever manipulations, forced addiction, and an incredibly stupid moose, Lilith was able to trick Sam into killing her... which just so happened to break the final seal to Lucifer's Cage."

Red is not religious, but the first thing out of his mouth is still, "My God."

"Look outside," Crowley instructs, and Red does. The sky is dark, even though it's well past ten in the morning. Thunder rumbles. Lightning streaks across the clouds. "There's a hurricane coming. There's been catastrophic weather all over the world. Random outbreaks of plague. And this is just the beginning."

Red's jet is going to be grounded. He'll need to find a hotel in the city. He can't stay at the bungalow with a hurricane coming.

"It's all over now," Crowley says, eyes dead. "There's no going back once it begins."

"That isn't a very can-do attitude, now is it?" Red asks. "You still have the Colt in your possession, I hope?"

"'Course I do."

"Then use it! Give it to the Winchesters, or use it yourself. It can kill anything, according to every ounce of information I've found on the thing. Perhaps it can even kill the devil himself. It would be a good start to stopping all this End of Times business. You can't give up now. That's never been who you are."

"You're saying I should go up against Satan himself? He'll squash me like a bug!"

"Only if you allow him to," Red counters. He rises to his feet, going to grab his coat from where it hangs by the door. "You're between the devil and the deep blue sea, Mr. Crowley. The time will come very soon where you have to choose."

When he looks back, Crowley is gone.

* * *

Six months later, Crowley shows up on Red's doorstep with a leather tote bag over his shoulder. Red's staying in a lighthouse in a small bedroom community outside of Seattle, called Mukilteo. When he saw it was up for rent, he couldn't resist. Crowley can't appear inside, because he's thoroughly warded the place against any and all supernatural entities... at least all the ones he can think of.

Judgment Day is coming. It pays to be cautious when the sky's about to rain fire down on you.

Red opens the door, Luger in hand aimed rather unceremoniously at the newcomer. However, when he sees it's Crowley, he lowers his gun. He doesn't holster it, though. He doesn't like that look in Crowley's eyes, like he's a cat backed into a corner. Never mind that parts of Crowley's suit are singed through completely, and his tie is stained with blood. He reeks of sulfur and fire. A long gash runs from his forehead down the side of his face.

"What happened?" Red asks without preamble.

Crowley swallows. "I chose," the demon coughs out, hoarse.

Red narrows his eyes. "And?" he prompts.

"Lucifer knows I want him dead," he continues, gravel-deep voice even rougher than usual. "And now all of Hell's after me."

They stare at each other for a few moments, and Red feels something bubbling up inside his chest. It takes him a span of five seconds to determine what it is.

It's pride.

He holsters the gun and heads off to alter his demonic warding. It's looking like he's going to be having a house guest.

* * *

Crowley hates tea.

Red doesn't care. He sets a cup down in front of the former King of the Crossroads, a chamomile concoction that a nun in Bolivia told him in her broken English was 'the Lord's way of healing'. Crowley looks like nine kinds of Hell (ha ha) and it's the best Red can do for him.

They sit in silence for a time, and Crowley sips his tea, gaze far-off. Red retreats to his bathroom and returns with a field surgeon kit. He doesn't like to sit still, not at times like this. He wants to know more of what happened, what's happening in the Real World, Crowley's world, but now isn't the time to push.

No. Not yet.

He's surprised that Crowley doesn't stop him when he starts methodically cleaning the laceration on the side of his face. He works slow and gentle. It's not the first time he's performed first aid, and it's not the last.

"You're not self-healing," Red observes.

"Overexerted myself," Crowley mutters. He drinks more of his tea. Only dregs remain in the bottom.

Red makes a sound to show that he heard him. He moves onto disinfectant. Crowley doesn't so much as blink when the burning liquid is splashed on his wound. Red doesn't know why he's bothering, really. It's not like a demon can get an infection and die. Immortality has its perks.

"I knew a fellow, once. In London. His name was Kerry. He lived in the basement of an old cafe on the banks of the Thames. I lived with him, for a time. Not that I had much choice, on the run from an organized crime syndicate as I was. He smelled like moth balls and Jim Beam, didn't talk very much. He came home every night, two-fifteen just like clockwork, and collapsed on the couch. He'd be covered in bruises, cuts, second-degree burns. An absolute _mess_. I'd fix him up every night, and when I was done, I would pour him a glass and ask him what happened. He never did answer me."

Crowley stares at the opposite wall, a veritable storm behind the green glass of his eyes.

"I wouldn't like to repeat that particular experience," Red continues.

The demon finally relaxes, ever-so-slightly, some life flowing back into his expression. His fingers dance on the edge of the cup. Red applies a bandage to the cut, pats it down. Crowley's eyebrow twitches with a familiar kind of annoyance.

"They burnt down my house," Crowley says. "I fought my way out. Barely."

"How did Lucifer find out your plans for him?"

"One of the Three Musketeers let it slip to a particular whore I have history with. She told Lucy, and now here I am."

Red settles down into the chair across the table, folding his hands in front of him. Crowley stirs the dregs in his cup with a teaspoon.

"The Three Musketeers," Red repeats. "The Winchesters, and...?"

"They're bloody angel. Castiel. Angel of Thursday. _Please_. Couldn't they have picked a more powerful one? Angel of Destruction? Angel of Fire? I hear Nathaniel's a hoot at parties." Crowley leans back in his chair, sticking a finger in the knot of his tie to loosen it, the entire bottom of which is torn to shreds. "I gave them the Colt, told them to empty it into Lucifer's face. Evidently it didn't go as well as I hoped."

"The Colt didn't work against him?"

"Not quite." Crowley retrieves a coin from the pocket of his ruined jacket and holds it up in the light. Its old, bronze, and looks eerily Grecian, though Red can't know for sure. Crowley pinches the coin, and Red is startled when it starts speaking.

"How did it _not_ work?" a gruff voice is heard on the other end, scraping machismo. "The damn gun is supposed to be able to kill anything!"

"Apparently not archangels," another voice says, male, but not nearly as deep as the other. This one sounds exhausted and furious, an odd combination. "That demon, he tricked us. He's probably right in Lucifer's pocket."

Red looks at Crowley.

"First is Dean, second is Sam," Crowley provides. "I slipped a listening device into that phallus on wheels they always drive around."

"Clever," Red compliments. It's something he would've done, in Crowley's place. Great minds... not that he's jumping to compare himself to the Crossroads King.

"I don't know if I buy that," Dean says. "Guy seemed desperate, and it makes sense, you know? No room for Crossroads demons in the new world order."

"If I find him, I'm going to stick Ruby's knife through his skull. We lost Ellen and Jo because of him."

"We'll kill Crowley, we'll kill Meg, and we'll kill Lucifer," Dean responds. "We'll kill them all, Sammy. We just... we need time."

"We may not have much time left," a third voice interjected, almost comically low. "If he's raised Death... it's only a matter of time..."

"That's the angel, Castiel," Crowley provides.

"Thank you, Mr. Sunshine!" Dean cuts across Castiel. "We'll figure out something. We don't have a choice."

"Our only hope now is finding God," Castiel states bluntly. "He is the only one who can stop Michael and Lucifer."

"Well, then we'll fucking find God!" Dean snapped. "Jesus, I'm just... I'm so sick of this crap. We just keep losing people."

"Never again," Sam said thickly. "We're not dragging anyone else into this, from now on. It's the three of us. We're going to have to go it alone, because... I'm not gonna watch anyone else die because of us."

Silence, for a time.

"I'm sorry," Castiel says quietly. "For Ellen and Jo. I know you two cared for them."

"Yeah, well. Sorry ain't gonna bring them back," Dean replies dismally.

Crowley releases the coin, and the live feed to the Winchesters and their angel ceases.

"They're looking for God," Red observes. "Do you think they'll find him?"

Crowley's eyes are dead when he says, "Not a bloody chance."

* * *

Red doesn't remember expressly saying that Crowley can stay with him, but the demon does, anyway, and he can't find it within himself to complain. However, when Dembe returns from visiting his daughter, he's less than happy to find the demon lounging in front of the fireplace with a glass of Craig in hand.

Red manages to talk Dembe down from devil-trapping and exorcising Crowley, but it takes a few hours.

Crowley, surprisingly, isn't even a bad house guest. Things seem supernaturally - or say, _demonically_ clean - and the demon even cooks when the mood strikes him. Or snaps his fingers and suddenly covers their dinner table in whatever cuisine fits his fancy for the night. Demons don't eat, but Crowley likes to indulge himself from time to time.

Crowley likes pizza. That's funnier to Red than it should be.

Sometimes Crowley will vanish for a few days, return looking about as hopeless as he had when he departed. Red also periodically disappears, but his business doesn't take him far. The Pacific Northwest is his area of interest, for the time being, as he tries to take out a human trafficking ring that's slowly gaining power. It's a largely contractual dealing, but he won't pretend he doesn't long to see the leader, a German man with a jaw that's been broken one too many times and ice in his eyes, bleeding out at his feet.

They come, they go, they intersect and have a drink. He's had far worse roommates in his time.

Crowley smells much better than Kerry did.

While Red does find sulfur deposits piled up in Crowley's usual places of rest (the demon favors an Eames chair on the third floor and a window seat on the first), he rarely smells the scent on the demon. Crowley wears a distinct kind of cologne, somewhere between cinnamon and wood smoke.

One night, a month into their odd living arrangement, Red stumbles through the door, soaked in blood and with a .22 round embedded into the meat of his shoulder. He's been separated from Dembe, and had to drive twenty miles with one hand on the wheel and the other trying to stem the rushing gush of blood from the wound. As soon as his feet hit the welcome mat, he collapses, black closing in around him like the swaddle of a warm blanket.

He wakes up fourteen hours later, feeling like everything was sucked out of him, and very little had been replaced. But when he manages to gather the strength to check his injury, he sees nothing but a faint white blemish.

Crowley makes him soup and tries not to look sheepish. He fails.

"You're much less of a demon than you'd care for anyone to believe," Red says after his umpteenth spoonful of bean and broth.

Crowley just glares at him and casually comments, "Guess you haven't tasted the secret ingredient yet. Potassium cyanide gives that extra hint of almond I just _love_."

It's after that day that Red is forced to acknowledge that although Crowley might own his soul, he is, in his own way, Red's friend.

He doesn't have many, so he supposes he should value the demon while the world is still turning.


	6. Chapter 6

"I would've rather Him not even be real."

Crowley and Red stare at the coin, listening to the dulcet tones of one Dean Winchester.

"I mean... if it had all been some kind of lie, if we'd gone up there and there'd been nothing behind the curtain, I could've lived with that. But for Him to be real, be watching down here on Earth, and just... not _care_? Say it's not His problem? That's just..." Dean trails off, unable to finish his sentence.

"Wrong," Sam finishes. "It's wrong that we care more than the guy who created... who created _everything_!" The younger Winchester exhales deeply, both emotional and physical exhaustion evident in the sound. "And now we're back at square one."

"Oh, we're way behind square one, Sammy," Dean replies tightly. "We had options at the start. The Colt, the God hunt, Gabriel. Now where are we? We've got nothing. Absolutely fucking _nothing_... I don't even know where to go from here."

There were a few beats of silence, until Sam responded with a solemn, "Neither do I."

Crowley pinches the coin, and the live feed to the Winchesters cuts. Red watches the demon, watches the lines draw on his face, hundreds of years of age shining through his comparatively young vessel. His eyes are tired and empty, the laughing spark in them dulled to almost nothing.

Crowley looks, dare he say it... hopeless.

"I get worried when you get quiet."

Crowley continues staring into space, fist pressed into the militantly set lines of his mouth.

"Tell me what you're thinking, Mr. Crowley," Red requests.

Crowley leans back in his chair and sighs deeply, still seeming a thousand miles away. "It's a dismal feeling, when you've thrown out plans A through Y and all you have left is–"

"–your very last resort," Red fills in. "That, at the very least, is something I can sympathize with."

Crowley rises to his feet, seemingly steeling himself. Crowley doesn't hold himself like he used to, proud with a rigid spine and regal poise in the tilt of his chin. Crowley remains proud, of course – only death itself can take that from the demon – but now he more strongly resembles a caged, wounded lion.

"So, I have to ask: what _is_ your Plan Z?"

The demon swallows with effort. "I'm going to break into Purgatory."

* * *

Red doesn't thinking breaking into Purgatory is a good idea.

At first, he just doesn't see the point– all he knows of Purgatory is the basic Catholic interpretation. A white, featureless in-between populated by those who had not yet earned salvation.

Red moves on from Mukilteo after depositing Erik Gerich's body in Puget Sound. The German's human trafficking business has been sunk spectacularly, and Red is proud to take both the credit and the healthy sum that hung over Gerich's head.

His next stop is Abu-Dhabi. One thing leads to another, and a fist fight in a tightly packed 'curios' shop in the slums leads him to a most helpful text: _Stamus ad Linem,_ a lore book on Purgatory.

 _Actual_ Purgatory.

Red's surprised to find that no human souls have ever stepped foot in Purgatory. It is, in fact, populated exclusively by dead monsters.

A graveyard for all things that go bump in the night.

He doesn't like the sound of it. What does Crowley even stand to gain from cracking open Purgatory? Does he plan to lead an army of dead monsters against Lucifer? What chance do mere monsters stand against the devil himself?

He wants answers, but after Crowley's dramatic proclamation that he was going to break into Purgatory, he vanishes, and Red can't get the demon to pick up his phone. The only memento Red has from their short time living together is the demon's coin, which still functions as a direct line to the Winchesters.

Red, unable to help himself, listens in on the brothers and their angel from time to time.

Dean: gruff, angry, ten pounds of daddy issues in a five pound bag, angst-ridden and with what sounds like a nasty case of suicidal ideation.

Sam: possibly even more angry than his older sibling, recovering addict, guilt complex, makes up for his brother's bravado with good old fashioned common sense.

Cas: monotonic, deadpan, brave to a fault, devoted life and soul to the Winchesters, and hopelessly, haplessly _lost_.

They're an interesting bunch. Red finds them undeniably compelling.

Almost six weeks after his last encounter with Crowley, Red hears the closest thing to good news he's stumbled across in a long time, straight from the mouths of Sam and Dean Winchester.

"Two rings, and we can stop Armageddon," Dean muses. "Wish someone would've told us that little tidbit sooner."

"What matters is that we know now," Sam responds firmly. "This is it. We found a way, now we just have to track down Pestilence and Death, and then lock Lucifer back in his Cage where he belongs."

"Oh, you make it sound so easy."

"We already took down War and Famine. What's two more Horsemen?"

Red calls Crowley once again, and simply says, "You may not need Plan Z after all. The Winchesters have found something."

Crowley doesn't appear immediately, but just as the sun sets on Abu-Dhabi, Crowley materializes on his balcony, leaning on the railing and staring out at the glittering expanse of the Persian Gulf.

Red notices immediately, in spite of being nose-deep in _Stamus Ad Linem_ and very close to drifting off to sleep. He has this way of sensing the demon's presence. His soul must recognize its owner.

With that uplifting thought, Red pushes the sliding glass door to the side and steps out to stand next to Crowley.

For a few minutes, they're quiet. The silence sits heavy, but it's not uncomfortable.

"So," Crowley says at length. "What is Buckwheat and Alfalfa's newest hare-brained scheme to stop the devil?"

"You're familiar with the Four Horsemen, I trust?"

Crowley gives him a withering look.

Red continues, "Well, it just so happens that the rings of the four Horsemen, when combined, form the key to Lucifer's Cage... and therefore, the key to stopping this whole unpleasant Armageddon business."

Crowley's expression transforms from mild interest to shock. "You're joking."

"I'm quite serious."

"The four rings... and the Winchesters should already have War and Famine's."

Red inclines his head. "They do."

"So that leaves Pestilence and Death." He sees more energy, more life in Crowley now than he's seen in months. "And I may not know where those two skeletal jockeys are, but I certainly know how to find out." Crowley smirks, plots and plans dancing in his stolen eyes.

"I suggest then, Mr. Crowley..." Red meets Crowley's gaze. "That you get to work."

Crowley's smirk transforms into a grin. "You're not so bad, you know that?" He pecks Red on the cheek. "For a human," he adds.

Red blinks, and Crowley is gone.

* * *

Red decides, ultimately, that if anyone can preserve the planet to fight another day, it's Crowley, the Winchesters, and Castiel. They have his utmost confidence.

That's not to say he isn't making plans, however.

"It's as secure as you're going to get," Mr. Kaplan tells him as she guides him through one of the deepest, thickest, and largest underground bunkers built for civilian use in America. Red needs a place for himself, Dembe and his family to hunker down, should things turn, well... apocalyptic.

And, of course, he needs a safe haven for Lizzie. He doesn't want to show up on her doorstep and ask her politely to come with him before fire rains from the sky and the earth is turned into smoking ruin, but if it saves her life, he'll have to suck it up and go with a less desirable reunion than he'd imagined.

"What kind of blast can it withstand?" Red asks, adjusting his sunglasses. Wholly useless underground, but he wears them as more of a fashion statement, anyway.

"Just about anything, according to the original owner," Mr. Kaplan says, adjusting her glasses and eyeing him down the length of her nose with open suspicion. "It should be able to survive any manner of nuclear event... within reason."

"Define within reason."

"Nothing's built to last through the United States' entire nuclear payload being dropped on top of it."

Red grimaces. In reality, that could be the exact equivalent of what's to come.

"You're hiding something," Mr. Kaplan observes.

"I'm always hiding a great many things. It's endlessly tiresome."

They continue down yet another gray, featureless hallway. Unbearably fluorescent lights blaze over his head, and he can feel a headache building in his temples. The underground bunker, located thousands of feet below a dry ravine in Montana, was once the bastion of a paranoid, Cold War-era millionaire with far too much money and free time at his disposal. Fifty-five years later, it stands as a testament to his belief that the end was nigh.

And maybe, just maybe, it is.

They enter out into a large room populated by an array of steel bunk beds, absent mattresses.

"This place looks like a prison. So drab, so institutional. I feel closed in," Red tells Mr. Kaplan. She looks up at him.

"If you didn't need this place, you wouldn't be here."

Red sighs. As usual, she's right. "How much?"

"Does it really matter?"

He buttons his coat, eager to go back outside and leave this cage under the dirt behind. "No. I'll take it. And Kate?"

"Yes?"

"Hire an interior decorator."

* * *

It's early when Red leaves his hotel in Butte and heads for the small airstrip where his private jet awaits him. He takes one step out of his hotel room, and he's almost instantly met with a blinding pain in the back of his head. Stars dance in his eyes, and he's down on the ground. He hears gun shots. He's unable to fight off the encroaching darkness, and he passes out.

When he wakes, his circumstances are not favorable.

He's bound, wrists chained behind his back. A shackle is locked tight around his right ankle and is connected unyieldingly to the floor. He's somewhere damp and dark; a disused basement, so far as he can tell. Dembe is nearby, hands similarly incapacitated, but minus the shackle. Unfortunately, having his legs free won't do him much good: Dembe is thoroughly unconscious, and the side of his skull is caked in blood.

"Hey! Look who's finally awake."

He's dragged unceremoniously up to his knees. Vision still blurry, it's cleared by the hard slap he receives to his cheek. There are two figures in front of him. One tall and thin with a shock of red hair, the other broad and stout and completely lacking anything on the top of his head.

The red-haired man grins at him. He's missing several teeth. "You're just who we wanted to see. You know why?"

"No, but I suspect you're going to tell me," Red groans, his voice hoarse from hours without having been used. How long has he been down here?

"You're pals with Crowley," he explains. "Me and Bosco here, well, we don't like Crowley much."

Red frowns. Demons. Fantastic. "You serve Lucifer."

"Look at that, Lyle," the broader demon comments. "He's all informed and everything."

"That's great news!" Lyle touts. "Because you're gonna tell us everything you know about Crowley. Where he is, what he's doing, and what his plan is. And if you don't, we're gonna carve out your liver and feed it to you. How's that sound?"

"Distinctly unpleasant, but of course, that's the whole point." Red's eyes flick between the two demons. "This surprises me, I have to say. Your loyalty to the devil."

"The hell do you mean, it _surprises_ you?" Lyle repeats, narrowing his eyes.

"Well, he's going to extinguish your entire race utterly if he wins this little head-to-head with Michael. Working for him seems counterproductive to your continued survival. Of course, that's just me. An old friend of mine used to say that if we all thought the same, no one would think much at all–"

He's cut off by a ham-handed fist landing a hard blow on his nose. He feels something snap, and he groans in pain, blood dripping down his upper lip. He tastes iron.

"Rude," he mutters. "I take it this isn't the open-ended part of the exam?"

"Shut up!" Lyle snaps. "Lucifer's gonna get those fucking angels out of the way, and we're gonna take over. _We're_ gonna get Heaven on Earth."

"How easily you forget that Lucifer himself is an angel."

"Enough," Bosco growled. "This is where you start talking, or we start chopping. Where's Crowley?"

"I haven't the faintest idea. Crowley doesn't keep me abreast of his plans. I'm hardly his confidante."

"Then why did he come running to you when he was exposed as a traitor?" Lyle challenges.

"You'll have to ask him. I wouldn't know."

Another blow to his face, this one sending him flat on the ground. The world spins around him, and his temple aches.

But, from this vantage point, he does notice something handy.

Dembe is waking up. Slowly but surely, his eyelids separate. He's dazed, confused, but he meets Red's eyes, and Red tries to convey a sense of urgency as best he can, before quickly looking away, so as not to draw attention to Dembe. Their captors are currently paying him no mind.

Mistake.

"Try again, or pick which finger you want to lose first," Lyle tells him. He kicks Red in the ribs for good measure, and pain arcs up his side.

"I've never found much use for the pinkie, have you?" Red asks. Dembe's eyes are fully open now. He's inching his chained hand towards his feet. Red doubts that Lucifer's lackeys were smart enough to search Dembe with a fine-tooth comb. His bodyguard has a whole menagerie of weapons hidden on his person, including a handy straight razor stored inside the lining of his boots.

Resourceful as always. What would he do without Dembe?

Lyle puts his boot on Red's ribs and levies his weight so it's crushing down on him. Red doesn't even give the demon the satisfaction of a pained grunt. He remains silent, trying to ignore the fact that his ribs are likely to break under this pressure, and _wow_ , does it hurt.

"Come on. You really gonna go through this just for Crowley? That bastard would stab you in the back the second he had the chance. He only looks out for one person, and that's himself. He probably knows you're here, knows what we're gonna do to you... and you can bet your ass he's not gonna come busting down the door to save you."

"I have no illusions about my relationship with Crowley," Red chokes out, his lungs screaming under the pressure as air becomes harder and harder to reach. "And there's one very deep flaw in your logic, I'm afraid."

"Yeah? And what's that?"

"I don't need Crowley to save me."

Red kicks out with his free leg and nails Lyle hard in the knee cap, sending him down on all fours. The weight on his chest is lifted, and he pulls in one blissful gasp just as Dembe threads his legs through the gap between his back and the chain of his handcuffs. He brings his hands up in front of him. He holds his straight razor steady in his right hand, and he lunges for Lyle, stabbing the razor into his carotid.

Unfortunately, Red knows that won't be enough to stop him.

 _"Exorcizamus te, omnis immundus spiritus, omnis satanica potestas, omnis incursio infernalis adversari_ –"

Bosco roars, launching at Red, but he manages to roll out of the way, using all of the limited movement the ankle shackle allows him. Bosco collides with the floor. Dembe rips the straight razor out of Lyle's throat, and in the span of a few fleeting heartbeats, its buried in the base of Bosco's spine. The demon screams. Red's surprised. Both of the demons' wounds are smoking, and they actually seem in pain.

Red continues the exorcism, and by the time both of the demons are back up and rounding on Dembe, they're mouths are forced open and black, noxious smoke pours from their throats. The demons' respective essences filter through the crack of a ground level window, and their meat suits collapse bonelessly to the ground.

"Excellent job, Dembe," Red breathlessly compliments his bodyguard. "You had all of your weapons consecrated, didn't you?"

Dembe nods. "It seemed wise."

"That it is. Would you mind...?"

Another nod. Dembe searches through Lyle's pockets. He locates the keys to both Red's restraints and his own. After releasing himself, he unlocks Red from both his shackle and his handcuffs. He massages his wrists and rises to his feet.

"I suppose I should've expected this," Red says. "It was only a matter of time before my... _involvement_ with Crowley led to less-than-fun encounters with Hell's denizens. I suppose we should be grateful Lucifer didn't send someone more capable."

Dembe just looks at him, dark eyes grave. "The demon is dangerous, Raymond."

"So am I," Red replies. "Just dangerous enough to survive what's to come, I hope."

Red's sentence is punctuated by the door to the basement being blown in, wood splintering and the iron hinges separating from the wall. What little remains of the door falls to the ground with a clatter.

Crowley stands in the doorway and stares at him. His eyes go from Red, to Dembe, to the abandoned meat suits on the ground.

"You're a bit late," Red points out.

"Apparently." Crowley looks incensed. "I come storming in like a white knight to save you, and you've already had all the fun without me. I'm hurt." He seemingly pats the air next to him, and Red hears snarling. "That's alright, boy. You can still have the bodies."

Dembe looks visibly shaken, backing away and muttering a string of curses under his breath. "Demon dog!" he spits.

A hellhound, eh? Red can't even find it within himself to be surprised anymore.

"Always so racist, Dembe. What do I have to do to get you to see the light?" Crowley smirks. "If you cut me, do I not bleed?"

Dembe doesn't dignify the snark with a response.

"I need a drink," Red says, wiping the blood off of his face. "You're buying."

"Fair enough."


	7. Chapter 7

**Chapter 7**

* * *

"So. How goes the hunt for the Horsemen rings?"

Crowley's eyes are fixed firmly on the TV. To Red's surprise, Crowley had requested they go to a sports bar for drinks. He explained that he needed to go someplace with a TV. A newscast played on the elevated flat screen, barely audible over the chatter in the bar around them. It shows footage of Chicago, which is about to get hit by a super storm the likes of which the city has never seen before.

"Depends on how you look at it," is the demon's distracted response.

"Chicago looks as though it's about to be leveled."

"Oh, it is," Crowley informs him. "Which is precisely why I'm here, and not there. Death is in Chicago."

"Death as in... _Death?_ "

"Yes. Dean Winchester is having pizza with him."

"Ah." He's reached the point where nothing can surprise him anymore.

"I've held the Winchesters hands, guided them to not one, but _two_ of the Four Horsemen... Death is the last stop. I gave the boy a scythe that he thinks can actually kill Death, but I very much doubt that it can, or that he could get close enough to use it before Death turns him to dust."

"I take it there's not much hope, then?"

"Death knows what he wants. If he wanted the Winchesters dead, they'd be dead. I can only assume the Reaper wants to bargain... with luck, Squirrel won't muck up their little negotiation."

"You're putting a lot of trust in him."

"Not really. I have rock-bottom expectations, so I can only be pleasantly surprised." He turns to Red, finally looking away from the TV. "We've reached the end of the line. A week from now, the world will either be a smoking ruin, or not. I've done everything that I can. All there's left to do is watch the Winchesters and pray to whatever deities that give a rat's arse that they can pull this off."

"But you don't think they can?"

Crowley forlornly swishes his drink around in his glass. "The first thing you learn in Hell," he says quietly, almost unable to be heard over the din of noise in the sports bar, "is that hope is the most dangerous, painful, and cruel thing in this universe."

"Because nothing hurts more than having it taken away." Red meets his eyes. "Is it true, that at the Gates of Hell **–** "

"Abandon all hope, ye who enter here," Crowley quotes dutifully. "The older demons say Dante was a real hoot at parties." He sighs, pushing his drink away. "It's also the best piece of advice I've ever gotten. If you have hope, you can lose it. I _don't_ have hope. But maybe, just maybe..." Crowley breaks off, listening to the anchorman.

 _"Now over to Jake with the weather... how's it looking over Chicago now, Jake?"_

 _"Well Tom, the strangest thing seems to be happening... it's almost as if it's clearing up! We were looking at a category five just a few minutes ago, but the winds are already dying down from sixty miles an hour, and the cloud cover is starting to break. We'll probably still get heavy showers tonight, but it looks like the super storm isn't so super after all!"_

Red smiles at Crowley, who's visibly relaxed upon hearing the news. "Do you believe in miracles, Mr. Crowley?"

Crowley shifted off of his stool, no doubt preparing to leave.

"Maybe," he says again. "Just maybe."

* * *

Four days later, Crowley visits Red.

He's never seen the demon so happy before.

"Oh, mate, you should've seen it!" Crowley raves, pouring himself another glass of Craig. They're in the penthouse apartment of an upscale complex in Amsterdam, and the city glitters below them, twinkling stars in the an expanse of black night. "All seemed lost, but then out of nowhere, the power of brotherly love or some tripe like that kicks in, and Moose takes back control and throws not just himself into the Pit, but Michael, too! Two archs, one stone. It was a thing of _beauty_."

"And you were there for all of it?"

"Ah... not exactly. I may have been scrying from a relatively safe distance."

Red just looks at him.

"What? I didn't think they stood a chance. I didn't want to get caught at ground zero."

"An acquaintance of mine, Ramses, he was a paramilitary guerilla in Andorra. He had a saying... Brave men fight wars, smart men plan them."

"Bravery is by far the kindest word for stupidity, wouldn't you say?"

"Not always, Mr. Crowley. Not always. Regardless, I'm happy for you, and for the world." He lifts his glass. "To the continued, stubborn survival of the human race."

"I'll drink to that."

So they do. Crowley grins the kind of grin that tends to make Red nervous.

As he nurse his drink, he asks, "What's next for you, then? Hell and Heaven alike must be in chaos, with their respective leaders gone."

"I don't give a damn about what's going on Upstairs. Hell, however... Hell is a complete disaster. Total anarchy. More so than usual." He takes a sip of his Craig, seeming quite pleased with himself. "Looks like someone is going to have to swoop in and take control." The demon smirks into his drink.

"Crowley, you old dog. You're going to take over Hell, aren't you?"

"King of the Crossroads... King of Hell. Seems like the logical next step up the corporate ladder, wouldn't you say?"

"Undoubtedly, but one demon trying to reign in an entire plane of existence..."

"One demon managed to stop Lucifer."

"I think we both know that you had a bit of help there."

"Yes, well, the angels tended to lend Charlie a hand, but notice the show wasn't called _The Angels and Their Friend Charlie_."

Red shrugs. "As always, I wish you the very best of luck with your demonic endeavors, no matter how unsavory they may be." Red gives him a tight, sardonic smile. "It does beg the question, though... did you help stop Lucifer in order to save the world, or did you do it so you could have Hell for yourself?"

Crowley smiles devilishly (ha ha) at him. He rises to his feet and straightens his lapels.

"Hmm..." he mused. "I guess we'll never know, will we?"

With that cryptic remark, the demon who would be king is gone.

* * *

Crowley's absence over the next few weeks doesn't surprise Red in the least; overthrowing Hell and taking the throne is no doubt a sticky and time-consuming business. His only true concern is that Crowley may not make it to the crown alive, depending on the kind of resistance he meets down below.

He tries not to think about the relative insanity of being worried about the well-fare of the demon who owns his ever-living soul. He doesn't know if he has horrible taste in friends, or if he's just a sucker for a good story.

Mr. Crowley is, without a doubt, a most _fascinating_ story.

Said story gets even more fascinating when roughly two months after the apocalypse that never was, Crowley finds him. But this time, as opposed to all of their previous meetings, he's not alone.

Oh, no. He has quite the companion.

"Raymond, meet Castiel. Castiel, meet Raymond."

Castiel is not what he expected; he's of average height, with a mess of poorly kept black hair and a five o'clock shadow. He wears a cheap suit with a backwards tie, along with a trench coat that's certainly seen better days. The only thing about him that comes across as even remotely angelic are his eyes. A bright, intense blue that seems to practically _glow_.

Heaven is in his eyes; the rest of him is relatively mundane.

Red offers his hand. "An honor and a pleasure," he says. Castiel simply stares at his hand.

"Shake it, you feathered oaf!"

Castiel glares at Crowley, but he does accept Red's hand and gives him a brief shake. "You are the... 'Concierge of Crime' that Crowley spoke of?"

Hmm. He hadn't known that Crowley adopted that particular nickname for him. "In a manner of speaking. You're the Angel of Thursday that I've heard so much about?"

Castiel nods, releasing his hand. "Yes. Crowley says you might be of some use to us, as you are bound to his will."

"Oh, I'd say our business relationship is a bit more consensual than that," Red says. He looks at Crowley, who just seems ready to burst into song. "What can I do for you, Mr. Crowley?"

"Cas and I, we've entered a bit of a... partnership."

"Oh?" Demons and angels, working together. He can't wait to hear why.

"I believe the human saying is... desperate times, desperate measures," Castiel says stiffly. "The last remaining archangel, Raphael, he intends to bring on the apocalypse. He wants to release Michael and Lucifer from the Cage and destroy the world. He must be stopped."

"Only problem is, he's an archangel. Awfully hard flies to swat," Crowley continues for the angel. "We need extra firepower."

Red sits himself down, crossing his legs and looking up at the two of them expectantly.

"I believe you remember our conversation about Purgatory?" Crowley asks.

"Vividly."

"Well... that plan is back on. Cas and I split the souls. I use my half to keep Hell in check and solidify my position as Devil 2.0, and Cas uses his to kill big brother and take over Heaven as the new and improved God."

Red turns his eyes to Cas. "You want to become God?"

"No," the angel grounds out. "No one is God. I wish only to lead the angels to something better."

Crowley rolls his eyes. "Whatever. Point still stands: he'll be the boss up top, I'll be the boss down south. Everyone's happy. The key is just getting to Purgatory and tapping into that little soul well of theirs. Which we would like your assistance with. Not that you get a choice, but we can pretend that you do."

"Who am I to refuse an order from the new King of Hell?" Red asks with half a smile. "Information is what you're after, I'm guessing?"

"Got it in one. Rare lore books are the name of the game. Any info you can find, we want. Also, we believe that some of the ancient monsters, the Alphas, they may be of use to us."

"Alphas?" Red echoes.

"Progenitor monsters, essentially. The first of each species. Keep an eye out, you see anything that looks like a big daddy monster, you call me, and we go from there."

"I'll see what I can do."

"Excellent." Crowley claps his hands together. "Oh, and Raymond?"

"Hmm?"

"This little deal between Cas and myself... best not say anything about it. People tend to jump to... _unhealthy_ conclusions."

"I can't imagine why," Red says dryly. "I won't breathe a word of it to anyone... your majesty." He uses the term with ample sarcasm, but Crowley still brightens at it.

"Then we have an understanding." Crowley winks at Red. "I'll be seeing you soon, darling."

Between one heartbeat and the next, angel and demon alike vanish.


	8. Chapter 8

**Chapter 8**

* * *

It doesn't take long for Red to start having his concerns about Crowley and Castiel's newest plot to save the universe. Mostly the same issues he'd had with it during Apocalypse Part I.

"Leviathan. Ring any bells?"

Crowley glances up at Red, nonplussed. Often times, Crowley comes to receive Red's weekly reports in person. They're in Gstaad, in a picturesque mountain retreat Red bought about a dozen years ago. It's one of his favorite safe houses, and also one of his most secure, tucked away into the mountains as it is.

"Some failed experiment, as I hear it." Crowley taps off the end of his cigar, a present from Red. His last trip to Columbia yielded some pleasant results. "One of those 'genocide-cures-all' kind of situations. God didn't want his new pets to become puppy chow for the Levis."

"If there's one thing you should know by now, Mr. Crowley, it's that nothing simply _dies_. Not in your world."

Crowley narrows his eyes at Red. "Mustn't beat around the bush, Raymond. My patience is rather lacking. That is to say... nonexistent."

"Leviathans, according to what I've read, were progenitor monsters. Long before the wolves, the ghouls, the vampires, the shapeshifters... and where do dead monsters have the tendency to end up, as you've been so kind to inform me?"

Crowley barely seems to be surprised. "I fail to see how this changes things. It's just more power. Why would I want to turn my nose up at that, hmm?"

"Because willingly accepting that much unbridled evil into yourself is bound to have less than positive consequences. You don't just come here for my dutiful reports. You come here for my opinion, for my outlook. My outlook, Mr. Crowley, is not a sunny one. Nor is yours if you choose to move forward with this plot."

Crowley leans forward, an undercurrent of something dangerous in the way he moves. "I suppose I'll have to remind you, since you seem so quick to forget..." Crowley blinks. His eyes turn a bloody, dark crimson. "I _am_ evil," he says sharply. "Far more than the Leviathan could ever hope to be! I'm the _King_ of Evil!"

"Hmph." Red isn't impressed by Crowley's display. Is he evil? Of course. But Crowley is not a wild, uncontrollable evil. He is not a thoughtless, blood thirsty evil. His evil, his personal brand, is much like Red's own. Precise. Calculated. Methodical... and never done without something to gain.

"That's it? _Hmph_?"

"Every hero has their fatal flaw," Red muses, puffing on his cigar. "I suppose the same can be said for villains."

Crowley is still staring at him with those red eyes.

"Your arrogance will be your downfall," Red continues serenely, perfectly aware that he's tempting fate by pushing Crowley's typical good humor like this. "I thought that Lucifer's downfall would have taught you never to underestimate your enemy. He underestimated _you_ , and now he's buried in the depths of Hell, likely to remain there for all eternity."

"Don't compare me to that temperamental child!" Crowley snaps. "We're not even in the same league."

"And yet, through the use of the Purgatory souls, wouldn't you essentially become him? Please, correct me if I'm wrong."

The question hangs heavy in the air between them. Crowley's eyes fade back to green, but are dark with anger.

"You wanted me to advise you on this matter, and here's my advice: you are in way over your head, old friend."

Red adjusts his fedora, leaning back in his seat and folding his hands over his stomach. Crowley seems poised on the precipice of something, some act, but soon enough the moment dissipates, as does Crowley's apparent rage.

Crowley rises to his feet. "This conversation is over. The next time I pop in, my darling, I strongly suggest you have a proper lead ready for me. You wouldn't like to see me disappointed."

Crowley's threat means little to Red, but he nods anyway. "As you wish... your majesty," he says, not without a hint of bitter sarcasm that he's positive Crowley picks up on.

Crowley watches him for a moment, then says, "Thin ice is a very dangerous place to tread, Raymond."

And then he's gone.

* * *

Red's network of contacts is as thorough as it is expansive. While he no longer has them followed directly, he does still keep tabs on the Winchester brothers.

He is very surprised to hear that somehow, against all odds, Sam Winchester is alive. Free of the Cage, and hunting once more– but without his brother along for the ride. Instead, Sam is in the company of the Campbell family, a well-known (in certain circles) group of hunters, led by Samuel Campbell, Sam's maternal grandfather who allegedly died three decades prior.

These are strange days indeed.

They become stranger still when the angel Castiel pays him a visit, sans Crowley. Castiel, unfortunately, chooses to do this in the middle of a high-stakes, illegal arms deal that Red is attempting to moderate. Dispositions are already volatile, so within seconds of Castiel's abrupt arrival, his vessel is decorated in bloody bullet holes, the victim of several hundred rounds of hollow-point ammo, discharged from a slew of assault rifles.

Castiel doesn't seem bothered. With a wave of his hand, the entire room collapses, leaving he and Red standing alone.

"Did you kill them?" Red asks, more out of curiosity than anything. He toes one of the fallen men with his loafer.

"No. I put them to sleep." Castiel takes a few steps toward Red. Involuntarily, he tenses. Demons and devils, fine... he's dealt with them his whole life, both literal and metaphorical. But angels? He'd have to be a fool not to be wary of something as powerful and unearthly as Castiel.

"I wish to speak to you," Castiel informs him in that gravel-deep growl of his.

"I gathered as much." Red gives him a tight but pleasant smile. "A simple telephone call would have been a simpler method but, I can't help but admire your approach." He gestured around the room. "I think you may have an unknowing flair for the dramatic, Castiel."

Castiel doesn't appear amused. "You have many resources at your disposal." It's not a question.

"Yes, I do."

"Are you willing to use those resources to help someone other than Crowley?"

"You and Crowley are working hand in hand, yes? I'm contractually obligated to acknowledge any friend of his as a friend of mine."

"Crowley is not to know of this," Castiel says immediately.

Red chuckles. Fascinating. "Ho-ho, now you've _really_ caught my attention."

"Do you know of Sam Winchester?"

"Oh Lord, yes. I've been watching over him for quite some time... almost like a guardian angel."

The joke seemingly sails right over Castiel's head. "I need you to keep close watch on him. I am... concerned. About his state of mind. But I cannot constantly shadow him. I have a war to fight." Castiel's hard features seem to soften, if only for a second. "But Sam is also important. He is my friend."

Poor Castiel's legendary weak spot: the Winchesters.

Red hums, seating himself at the head of the table and crossing his legs. The former occupant is passed out on the floor at his feet. He steeples his fingers and considers Castiel. "Define watch," he requests.

"Observe and report. To me, not Crowley." Castiel fumbles around in his pocket, then pulls out a cheap Trac phone. "Via... cellular phone. I will provide you with my number."

"I find it interesting that you would approach me of all people with this, given my loyalty to Crowley," Red muses as Castiel hands him his cell phone.

"Is what you feel for Crowley truly loyalty? He owns your soul indefinitely. He has made you out to be little more than a slave."

 _Oh, has he?_ It isn't a wholly inaccurate statement, but Red still doesn't like the sound of it. He is no one's slave. "So. A slave to a demon, or a slave to an angel."

"I am not asking you to pledge yourself to me. I wish only for you to do as I have requested... and to not inform Crowley of your activities, or this conversation. In return, I will... I believe the human saying is that I will owe you one."

Now this is the kind of bargain he can get behind. An angel of the Lord owing him a favor? The possibilities are endless.

"Be careful who you promise favors to, Castiel. Wouldn't want you to make a deal with two devils, now would we?"

"My deal with Crowley is one of necessity, and it exists on my terms and my terms alone," Castiel insists, his feathers evidently ruffled by Red's statement.

Red can't help but scoff at that. "I think you and I both know that isn't how our dear Mr. Crowley operates." Red takes out his own cell phone and quickly taps in Castiel's number before returning the phone to its owner. "Nevertheless, consider our arrangement made. But bear in mind... I will come calling. I suggest you be ready and willing to fulfill your end of our bargain when the time comes."

Castiel narrows his eyes at Red. "You should watch your tone. I could annihilate you with a thought. Erase you from the face of this universe as if you had never existed at all."

Red laughs. "Ah, such is life, but I've seen far worse than you in my time, Castiel. You'll simply have to be, well... _more_ , if you ever hope to intimidate me."

Of course, Castiel does intimidate him, but if there's one thing his life has taught him, it's one undeniable and constant rule: never let your fear show. Feel your fear, embrace your fear... but _don't let it show._

Castiel stares at him like he can't wrap his mind around this audacious human, his sheer arrogance. He opens his mouth to respond, but then seems to decide otherwise, shaking his head in what almost seems like exasperation.

"I expect to hear from you soon."

Castiel disappears with the sound of flapping wings, and Red is left alone in the room full of sleeping murderers. He smiles to himself, because this is it. This is where he is most comfortable. Playing both sides, Heaven and Hell, ruling the entire board from behind the scenes.

It's time for the puppet to become the puppet master.


End file.
